As seen in Crains "A San Francisco firm's IPO pays off for Chicago investors"

Last week's IPO of San Francisco-based DocuSign created a big splash that rippled all the way back to Chicago.

One of the big winners in the $629 million deal was Second Century Ventures, a strategic venture fund run by the Chicago-based National Association of Realtors, which was the fourth-largest shareholder. It sold 1.6 million shares for $46.4 million at the $29 IPO price on April 26. Its remaining stake of about 4 million shares is worth about $165 million.

How did association get in so early? It did a small investment and an exclusive partnership with DocuSign to offer its software for digital signatures to member Realtors, according to securities filings. It's quite a home run for Constance Freedman, founder of Chicago venture fund Moderne Ventures. It was her first deal when she was running Second Century Ventures.

But she's not the only local winner in this deal. DocuSign acquired Cartavi, a Naperville-based software startup, five years ago. Investors Chicago Ventures and OCA Ventures each ended up with DocuSign stock that I'm told is worth several million dollars, producing returns in the range of 15 times their investments. Chicago Ventures and OCA declined to comment. Other investors included Pritzker Group Venture Capital, FireStarter Fund and Fieldglass founder Jai Shekhawat.

The deal also paid off for Glenn Shimkus, Cartavi co-founder and former CEO who recently joined legal software firm Relativity as head of product and user experience. "It's been a wonderful exit, not quite a Facebook-type explosion but an incredibly solid return," said Shimkus, who says he will be gathering with investors for a celebration in the coming weeks.

The deal paid off in other ways, too. DocuSign still has a growing office in the western suburbs with about 75 people.